Patent GB-876526-A (GB)
Title: Process for the production of new aminobenzoic acid derivatives and their use in pest control
Filed: 1958-12-17
Abstract: The invention comprises compounds of the formula <FORM:0876526/IV (b)/1> where Ar represents a phenyl, phenoxyphenyl or phenylmercaptophenyl radical, which radical is substituted by at least one halogen atom and/or trifluoromethyl group and which may be further substituted by a methyl or alkoxy group containing up to four carbon atoms, R1 represents an alkyl radical containing 1-4 carbon atoms, R2 represents hydrogen or an alkyl radical containing 1-4 carbon atoms, hal represents chlorine or bromne and n is a whole number from 1 to 4 and where the total sum of halogen atoms and trifluoromethyl groups present in the molecule as substituents on the aromatic rings is greater than 2 and preferably at least 4.  The compounds may be prepared by (1) reacting an anthranilarylamide of the formula <FORM:0876526/IV (b)/2> with an alkyl sulphonyl halide R1SO2hal, the reactants being chosen so that the product contains at least three halogen atoms and/or trifluoromethyl groups as ring substituents and if desired, treating a product in which R2 is hydrogen, either in the presence of an acid binding agent or after conversion into an alkali metal salt, with an alkyl halide or sulphate containing 1-4 carbon atoms; (2) reacting in the presence of an acid binding agent a halide, anhydride or ester of an N-sulphonyl-anthranilic acid of the formula <FORM:0876526/IV (b)/3> with an arylamine ArNH2, the reactants being chosen so that the product contains at least 3 halogen atoms and/or trifluoromethyl groups as ring substituents, and if desired, alkylating compounds in which R2 is hydrogen as before and (3) reacting a compound of the formula <FORM:0876526/IV (b)/4> which contains less than 3 halogen atoms and/or trifluoromethyl groups in the molecule with chlorine or bromine until so many chlorine or bromine atoms have entered at least one of the aromatic rings of the molecule that the total sum of halogen atoms and/or trifluoromethyl groups in the molecule reaches at least three.  Examples describe the preparation of 2-methane sulphonamido-3,5-dichlorobenzoic acid-31,41-dichloranilide and its N-methyl derivative, the corresponding 31,41,51-trichloroanilide and the corresponding 4,5-dichlorobenzoic acid 31,41-dichloroanilide and N-methyl derivative by method (1); 2-methane-sulphonamido-5-chlorobenzoic acid-21,31,41,51-tetrachloroanilide by method (2) and 2-methane-sulphonamido-5-chlorobenzoic p  acid-31,41-dichloroanilide by method (3).  A list of the other products which may be obtained by these processes is given.  2-Methane-sulphonamido-5- chlorobenzoic acid is prepared from the corresponding anthranilic acid and converted to the acid chloride.  o-Nitro-benzoic acid 3,4-dichloroanilide is prepared from the benzoyl chloride, reduced to the corresponding amino compound and chlorinated to give 2-amino-3,5-dichlorobenzoic acid-31,41-dichloroanilide. 3,5-dichloroanthranilic acid is reacted with phosgene to give 3,5-dichloro-isatoic acid anhydride which is converted to 2-amino-3,5-dichlorobenzoic acid-31,41,51-trichloroanilide. 2-Methylamino-4,5-dichlorobenzoic acid is similarly treated and converted to the 31,41-dichloroanilide.ALSO:Keratinous material, e.g. wool, is moth-proofed and dry cleaned by means of a composition containing a suitable dry cleaning solvent and a compound of the formula <FORM:0876526/III/1> where Ar represent a pheny, phenoxyphenol or phenylmercaptophenyl radical, which radical is substituted by at least one halogen atom and/or CF3 group and optionally by a methyl or alkoxy group containing up to 4 carbon atoms, R1 represents an alkyl radical containing up to 4 carbon atoms, R2 represents hydrogen or an alkyl group containing up to 4 carbon atoms, hal represents chlorine or bromine and n is a whole number from 1 to 4 and where the total sum of halogen atoms and CF3 groups as ring substituents is at least 2.  In an example a solution of 2-(N-isopropylsulphonamido)-3,5 . dichlorobenzoic acid . 31,41-dichloroanilide in methoxyethanol is mixed with a benzine fraction (Diluan S) and woollen articles dry cleaned in the usual way.ALSO:A composition, suitable for the protection of keratine material from injurious insects comprises a carrier and a compound of the formula <FORM:0876526/VI/1> where Ar represents a phenyl, phenoxyphenyl, phenylmercaptophenyl, which radical is substituted by at least one halogen atom and/or trifluoromethyl group and which may be further substituted by a methyl or alkoxy group containing up to 4 carbon atoms, R1 represents an alkyl radical containing 1-4 carbon atoms, R2 represents hydrogen or an alkyl radical containing 1-4 carbon atoms, Hal represents chlorine or bromine and n is a whole number from 1 to 4 and where the total sum of halogen atoms and trifluoromethyl present in the molecule as substituents on the aromatic rings is greater than 2 and preferably at least 4.  The active compound may be made up with the usual aqueous or non-acqueous liquid diluents and surface active agents may be added.  In examples active compounds are dissolved in (1) aqueous NaOH with some alcohol, (2) dimethyl formamide, water and emulsifier, and (3) methoxy ethanol and a dry cleaning solvent. The compositions are particularly suitable for moth-proofing wool.